Both of Homeister's parents were jockeys, and as a result she grew up riding horses. Her mother is now a horse trainer at the Calder Race Course, where Rosemary won her first race as an apprentice jockey. In 1991, she briefly attended Broward Community College but left to develop a career in racing. Homeister started her career working with horses as an exercise rider and breaking yearlings before beginning her riding apprenticeship in 1992. She was successful that year, becoming the first woman to win the Eclipse Award for Outstanding Apprentice Jockey in the United States. She was originally the runner-up, but winner Jesus Armando Bracho from Venezuela was suspended, then surrendered his award for falsifying his racing papers. Two years later, she went to the awards ceremony to accept the award. Since then, Homeister has won more than 2000 races at tracks in Texas, New Mexico, Oklahoma and along the East Coast of the United States from Florida to New York. In 1995, she and her mother were profiled by CBS News Sunday Morning. In 2000 and 2001, she was the United States leading female jockey in wins. In 2001, she was the first female jockey to win the Clasico del Caribe conducting the Panamanian filly Alexia. In 2003, she became only the fifth woman to ride in the Kentucky Derby, finishing 13th aboard Supah Blitz in a race won by Funny Cide. Homeister retired in November 2004 after thirteen years of competition, having won 1,726 races from 12,907 starts. However, she returned to racing in June 2006 and on September 3 of that year was inducted into the Calder Race Course Hall of Fame. As of December 2006, she is divorced from jockey José Ferrer, according to an interview she gave TVG Network's Lady Luck. At Tampa Bay Downs on December 18, 2008, Homeister won her 2000th race. On February 11, 2011, she announced that she was pregnant and would not ride for an indefinite period, and then returned to race riding in 2012. She rode the filly Include Betty in the 2015 Kentucky Oaks.
Racing awards and achievements
Rosemary Homeister has won 102 Stakes races, four being Grade 2s. She has had been many firsts in the racing world. Winning the 1992 Eclipse Award as an outstanding apprentice jockey and the first and only woman to be invited, ride in and win the Clasico Del Caribe on a filly, named Alexia, against all-male riders and horses.
1992–1993 – Leading Apprentice Jockey at Monmouth Park
2009 – December 17, won 4 races out of six on the day at Tampa Bay Downs
2009 – December 19, Honored with Jockey of the month at Tampa Bay Downs
2009 – November, winner of the $150,000 Valedictory Stakes with Cloudy's Knight in Woodbine, Canada
2009 – December 26, won the $150,000 Grade 2 W.L. McKnight Stakes on Cloudy's Knight.
2010 – February, won the $75,000 Suncoast Stakes on Diva Delight for trainer David Vivian –
2010 – February 20, won the $150,000 Tampa Bay Breeders Cup Stakes on Karelian for trainer Rusty Arnold – beat Gio Ponti by a nose.
2010 – March 13, won the $175,000 Florida Oaks Stakes Grade 3 on Diva Delight –
2011 – August 21, gave birth to a girl named Victoria Rose
2011 – November, won on her second race back for trainer Eric & Kay Reed on Eden Star.
2012 – Third Leading Rider at Arlington Park – first year riding at this track.
2014 – won over 2,700 races
2015 – winner of the $300,000 Fantasy Stakes on Include Betty
2015 – retired on September 28
After retiring from horse racing Rosemary took her passion in the Health and Wellness industry by becoming a Certified Personal Trainer and Fitness Nutrition Specialist. She went on to compete in Bikini Fitness winning her first show and then competing internationally to finish second among top competitors.